Paragliding the Matterhorn: Startup Symbolism

Northern Italy (ATP Finals Trip - Part 2)

Landed in Venice, the city of water.

 With ferries, I got as far West as to overlook the edge of the Adriatic Sea.

A very historic city, I wanted to witness the land of Marco Polo and complete his reverse route through Northern Italy by heading West (Part 1).

I rode the Le Frecce high-speed train to Milan for the ATP NextGen Finals - Travel Photos.

ATP NextGen Milan

That pitstop at ATP NextGen in Milan was showcasing the top young stars (aged 21 and younger). Serendipitously, I met up with the mom of our hometown San Diego Open champion Brandon Nakashima! My mother was also born in Vietnam originally.

I stayed a couple days to see the famous Domo and Last Supper. Milan is a very fashionable and hipster-friendly city

The ATP NextGen Arena location itself looked like a large indoor high school gymnasium. Lots of Italian kids and families. Fans enjoyed the flashy light and sound show. It's the junior version of the ATP Finals event.  He concluded the season by winning the tournament, beating several top players along the way.

A couple of days left before arriving for the ATP Finals in Turin...I still needed to decide where to go next. My eyes scanned the map and the weather forecast.

In that region's shoulder season, November is typically known for rain and cold weather. Not yet cold enough for snow, yet too cool for most fairweather tourists.

Enter Hemingway - Stresa, Italy on 11/11 @ 11AM

From the Stresa central train station, I made my way to an AirBnB real (modernized) Italian castle with the original exterior on 11/11 - Armistice Day. It was the day when the guns fell silent at the end of World War 1.

Overlooking the island, I spent the night across Isla Bela. It was near the hotel viewpoint where Ernest Hemingway wrote "Farewell to Arms". With no car, I decided to cover the entire area on foot. Its downhill roads weren't designed with sidewalks in mind.

The following day I decided that instead of going South back to Milan again, I would detour North towards Switzerland. Near the Italian/Swiss border was a lifetime bucket list.

The Mountain peak in the Swiss Alps called the Matterhorn was pinned with a heart. Like a siren beckoning me on my Google Maps, it called out: Matterhorn!

Paragliding for the 1st time. Soaring through Zermatt.

Mapping and Mountaineering

"No matter what you do, building a start-up will be a very challenging journey…if you don’t start with enough passion, you won’t get to the other side. If you don’t fall in love with the problem, you simply will not be able to get through the journey.” 
- Uri Levine (Co-Founder of Waze) "Fall in Love with the Problem" (2023)

The key luck factor was the weather forecast. It was nothing short of a miracle in November to get clear skies and 50s a high temperature! With just a short 48-hour window, it was now or never. Time to go for it.

Eagle's Nest

I booked a last-minute little AirBnB. One only crazy backpackers (or last-minute cowboys like me) would even consider. With this once-in-a-lifetime chance, the detour is the adventure. The Obstacle is the Way.

This began the first leg of many to reach Zermatt (basecamp for the Matterhorn). Several trains, buses, shuttles, and 2 lifts later - I would reach snow. The start of a long hike to reach the final jump point.

Lost in Translation

At Stresa's main train station, nobody was working at 6:30 AM. I had to rely on using the automated Italian train ticket machine. I typed in my destination, "ZERMATT." The error screen flashed back "No route found". I tried several times again with the same result: "No route found." Uh oh.

I pulled up Google Maps again and saw I'd have to make a few transfers. Maybe this system would only take me halfway? Reaching Zermatt would take a few different national transportation systems (an Italian Train, then a Swiss Train). I ate a quick Italian cafe breakfast sandwich, then waited outside.

It had two platforms - A and B.

15 minutes left. Still no staff working yet inside the station. Nobody was even inside the window counter. So I go outside seeking assistance from one of the other passengers who would likely know. I found one Italian lady also waiting. She stood confident, posed like a regular daily rider.

Me: Excusi. This train? To Brig? (pointing to Google Translate)
Her: "Brig? No, you need to take the other platform..."

She pointed me to go to the other side.
Unfortunately, that "other platform" was for regional trains only. My 30 Euro ticket was supposed to be the express one. But because of common rail delays (I was told), it would be running 15 minutes behind schedule that morning. This is where things start going South.

So I even check the printed train schedule on the sign post. It listed train's arrival at Stresa with the departure times. The difference was only 4 minutes off from the ticket's actual time. Close enough, or so I thought...

Getting on the Wrong Train

So the Platform B train arrived. I hopped on. Immediately I should have noticed something was wrong. The creeky rail car doors were so old it barely even slid wide open as one rider tried getting off. Inside, the car was nearly empty. Dusty windows, like those from an old black and white movie.

Leaving my bags there, I headed to the front of the train for help. I don't see anyone. I needed to get off! Maybe I could still run back to the station and get back in time? With my luggage too? No way.

Hopping forward, the train's next adjacent 4-5 cars were equally vacant. I slid open cart doors, one after another. All identical. Empty. With a knot in my stomach, I quickly realized that this was the regional train! It would require at least 8 more stops to go. Definitely missing my transfer in 30 minutes.

Upon reaching the first rail car, I found an elderly gentleman who spoke English. He put down his newspaper and kindly explained the train I should have been on was platform A. He looked at his watch - yes it should be passing us soon.

There, he pointed at the much newer, much faster, speeding white blur that was my train overtaking us. I thought the tortoise always wins?

My best option was to stay on until the main station.
I could rebook once I arrived at the main junction town of Domodossola.

Accepting my fate, I sat back down and enjoyed all the little towns and cows along the way.

Switzerland's Ride to Ski Resorts

After my transfer from Brig to Riga, I noticed a big contrast between the surroundings.

This was Swiss ski country!

It was still early in the season, yet so many passengers were going there for a weekend mountain getaway.

The Italian train staff at the station advised me that I need not bother with a refund. Just show them your (Trenitalia) stub; she assured me it should be fine. Nope.

Swiss trains were noticeably cleaner, quieter, and well-staffed.

Clear, large-paned windows reveal Nature's glory.

Tickets, please!

Young train staff stood posted at the SBB red trains. No getting around them. They wore satchel bags, serving as mobile kiosks. They were well-armed with point-of-sale card readers around their necks and pockets full of literature. I showed them my old stub and explained the simple mistake. But they weren't messing around.

Sorry. You can't board Swiss trains with Italian tickets.

Ah, lost in translation. I took out some Euros.

From all these extra detours, I lost some weight. So did my wallet. :)

On board the train, I received an Airbnb text from my host.
I had notified him that I'd be running an hour behind schedule.

The text reads:
"no problem."

"Hey, do you still want to go paragliding?"
"the paragliding pilot, Bruno, will meet you at Grampi’s."

My host knew a local guide named "Bruno" who could take guests up if the weather permitted. For days, we had exchanged messages. This flight option would be only possible if wind conditions were favorable. It was essential to check the local weather forecast from Tarasch or Zermatt, not outside.

Apparently, fate wanted me to go fly on that day.

(Skip to Story: Bruno and the Air Taxi)

Scaling up is one part Grit - but two parts Audacity.

Arriving is easy. Anyone can enter a gift shop.
Overpay for a logo magnet or postcard, and say you were there.

The rich come to the ski resort town of Zermatt and take a lift ticket straight to the top. Reaching it on foot, like my Stanford mentor did as a youth - is another matter.

Fundraising angel or seed capital rounds takes enormous perseverance.
It is an ice-cold wind tunnel test of facing repeated hurdles, uncertainty, and rejection.

With previous large group vacation planning over the years, I had wasted so much time. Pitching, explaining, educating, and then trying to persuade others to bring them along. You'll never make everyone happy - nobody is born an avocado.

Change is hard. New is risky.

Due Diligence

To truly separate between the hype and the reality requires you to put boots on the ground with due diligence. In March 2021, I flew red-eye from San Diego to Miami cross-country to arrive Day 1 for the filming and meet the entire film crew of TopCourt. Pitch Decks only tell you so much.

You need to go the extra mile and be able to bring yourself there. Show that you're willing to grind out the hours alongside the team to understand how operations work. No armchair QB's if you're in it with your own post-tax dollars.

CES 2023 Eureka Park - Gallery of Flops - the Startup Graveyard

In the book "Cold Start Problem," Andrew Chen describes the hundreds of thousands of new startups in the US annually. Linking sufficient self-propelling supply (the Hard Side) with increasing demand is often the challenge in Network Models.

Imagine it's like empowering the East and West coast teams of the Transcontinental Railroad to connect at Promontory, Utah. Done successfully, it linked the two halves of America, its coast, and thus also a nation.

Solving the Hard Side: building the first Unicorn - the steel Horse and the magic Horn.

“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.” - Beckett

How many strangers or VCs will take the plunge with you? Can you get sustainable funding. Will you continue to iterate, test, fail, and repeat as long as it takes?

The "Desert of no Traction" - Saraha of Startups.
After the honeymoon phase, there are sometimes long lulls. Weeks or months where revenue flatlines. This period tests the Founder's heart. You are sometimes blind with no good KPIs to find progress.

At that point, you can only put one foot in front of the other - day in and day out. Until you finally hike it out alive or your cash tank runs dry. This is the sacred test of the Soul of a start-up.

Beware of false promises - the checks that can't be cashed.
Some will tell you that your idea sounds good when you're presenting. Then disappear. Nobody doubts your conviction. But when it comes to crunch time, how many would put down their own money to go on that one-way ticket with you? How small things are handled is often a microcosm of the large decisions. 

"If you don't like extreme sports, maybe a start-up is not for you" (Uri Levine, page 36)
Don't listen to the naysayers and fearmongers - they reject you, then ignore you, then fear you.
Anchors are everywhere - ready to ground you down to their level.
Prepare for people ready to tell you it won't work and why you're crazy.

"People don't like change, and your new start-up is a change." - Levine

Gathering light feathers for a pair of wings.
Build a solid team that reinforces the other like bonding glue.
It takes a leap of faith, some luck, and being able to endure the long ride.
You must risk stepping off the safe path and go forging into the wild.
The secrets of real discovery await you in these dark woods (of Tal).
"The door is going to open for a slipt second. 
Whether you choose to jump through it or not, it's not going to be there very long." 
- James Cameron (MasterClass)


Zermatt's Swiss graveyard. Miners who paved the way and paid the cost of conquering a Mountain.

Climbers don't get to pick their destiny - conditions pick the climber...

Great tennis champions become legendary because they faced and overcame giants themselves. Immortal matches are those created from facing adversity at its peak. Nobody really remembers straight-set Finals as well as 5-setters.

Before the trip, I saw the 14-day forecast. I knew I only had a 25% chance of making a launch window. I did not even book any lounging plans ahead of time. I did not know after Milan if there would be another change of plans. It's the dreaded equivalent of a "rain delay" for tennis.

Often, the Alps forecast is grey with a rainy mix of gloom in November.
The Christmas Markets would be a couple weeks away.
I studied the forecasts and had a backup route if things go wrong.

Always understand the odds, kid - even if you choose to ignore them. (Hans Solo)

Eternal Optimism - the humility of sponsorship, fundraising and eating your own dog food first

As most athletes, we constantly train and prep everything to give the best chance to go.

In tennis, you prep your footwork before the ball approaches - even with a 5% chance it will land. You must be ready just in case. You put in those long hours in the gym before spending those final few seconds striking the ball.

I bought my train ticket as far as Stresa and then took a day-to-day outlook to see if I could ascend or turn back. Since I had a chance, I decided not to waste time and booked the first train in the morning. These are the moments you cannot always plan for.

If you don't believe in yourself, nobody else will back you. Out on the singles court, you are your own psychologist. You have to pay your own way when you start out. Can you even afford a coach and hitting partner? Will you book a hotel room if you don't expect to make the 2nd week?

How often you see journeyman pros outside the top 100 seeking sponsorships - even their clothes look like a NASCAR racing suit of Frankenstein patches for whatever they can afford.

Travel teaches you how to rebound from setbacks.

Getting delayed an hour put my timeline entirely off the rails. My connection west at Riga was now pushed to the right. I had to buy a new ticket on the Swiss train to continue forward.

Delays like catching the wrong train can be out of your control. Don't let it derail your mission.
Still, you should plan forward because your premise and goal have stayed the same despite that roadblock. It is all part of the adventure, and even when things go off-script, it makes for great stories later.

Getting rejected, denied, blocked, and ignored by normal.
It's why my HS Physics teacher had us learn to cold call parents in high school.

(We don't talk about) Bruno and the Air Taxi

"I'm Bruno. Follow me - we have no time to waste if we are going to catch the next train up!" When I arrived at the meeting point, he said this would be a hard push if we wanted to make it.

So, immediately before he even fully discussed the price or details, he had me wheel my luggage to his ski office about a half-mile away. Luckily, he had an extra pair of snow boots and a parka he could lend me before we ascended.

Bruno imparted a strong sense of urgency and determination. Barely any time for cordial greetings or learning much more than my name or where I was from, we were off. I had some doubts. Did I have enough warm layers? What if my camera came flying out of my hands? Could we make the train?

Trapeze artists take their hands off - fly or die; there is no try...

Reaching that next rung requires letting go of your safe hand.
Intuitively this feels crazy to give up what is well-known and secure.
Just like in rock climbing (free solo).

To be a great entrepreneur:

Be ready to trade that "bird in the hand" for that "bird in your heart."
It is with blind faith that you can forge across the midnight current.
A solo journey that each man must decide to take alone.

I've seen a former wall street day trader try to go pro in tennis. Go pro or go bust, he said.
No worrying or ruminating about worst-case scenarios or past mistakes. They won't do you much good now. Don't panic. The skill in the Trapeze is being comfortable. At that moment of no momentum. It is a silent pause. A weightless release. Timing is by feel, as much as it is by sight.

Sometimes, you want a seasoned guide who will push you.
Let go of the bar! Reach for the next rung.
It is there. Even when your heart stops. Reach.

A coach must show you that it has been done before.
It can be done on this day - as it was by someone else yesterday, as it shall be done again tomorrow. So why not you? You must have faith that you are that someone. You can get the funding to continue once you arrive at that drawbridge. Conquer the dragon within.

Unlike a steady W2 salary job - this is not the clean, manicured path where you go to work, earn a steady paycheck, and retire. Nobody hands you an SOP and employee handbook.

Glory is your own. The setback is your own. No retreat.
You are both the point man and the last man.

Like the paraglider, you pack all your gear to go up.
Prepare your re-entry back to Earth.
Return. Smoothly or suddenly.
But you will return.

With the one-way ticket,  move up.
Don't plan on returning the same way as you went up. "Burn the boats." 

“The cowards never started and the weak died along the way. That leaves us, ladies and gentlemen. Us.” - Phil Knight, Shoe Dog
To summit life's tallest mountains, you need to shed some weight.
That weight is usually some combination of fear, weakness, inertia, and resistance.

Alas, not many fans can join you on this quest.
Not from lack of desire, but lack of oxygen.

Up where only a thin sheet of nylon separates you from oblivion.

Some ask: why attempt to paraglide on your first Matterhorn visit?
The easy road is to ride a gondola, enjoy the vista view, and then return home with a selfie.

Why the Moon? Speech by JFK

Precisely because I knew I would not be here again.
The challenge is fulfilling the quest.
To come this far and fail is not in me.

Don't look back one day only to regret not maximizing that potential.
Knowing I was only there for that one day.
Be proud of going for it, for trying where others have turned back.

Para-Waiting: lessons in patience from Fishing

Taking small steps and being content with incremental progress is not the mindset of market scouting as a startup entrepreneur. It is about shooting for the moon or bust, going for the proverbial hockey stick curve.

We prepared the sails when we trekked another 20-30 minutes to the cliff's edge. Simply admiring the view would not allow us to catch that critical bit of wind to get off the mountain safely. The equipment rollout took another 10-15 minutes of detailed preparation.

Never step on my lines, I remember Bruno warned. He wasn't kidding.
It's just thin, colorful threads that keep a shallow plastic foil up to defy gravity. Only those small threads separate a smooth descent from a death spiral.

I equate this nervous time of uncertain anticipation to the negotiation exit phase in startups.
It is a game of chicken with the wind and nature. Sometimes you prep everything perfectly and get all the details right, yet you don't get your shot. Sometimes it is the right idea at the wrong time. All you can do is put it all out there and pray to the Wind Gods for the fateful breeze.

Ready to cast into the falling tide.

To quote Arthur Brook's book - Strength to Strength - you must be ready to "cast into the falling tide." During the receding waves, when everything is going out - that's when the fish are biting.

As counter-intuitive as it may seem, this is the best time to go fishing.

The only mistake you can make is "not having your line in the water."

Embrace running against the wind.

All of a sudden, I heard the command.
Start forward, ok now, faster, faster!
I paced forward with the harness around my waist.
After 20 or 30 yards, I saw the edge round off and drop down.

Accepting the purchase agreement to sell your company gave me the same halting feeling of guilt. On the one hand, you have your baby. On the other hand, you have to let it graduate and grow.

It's like waiting for your college acceptance letter.

Waiting weeks or months. Assigning a dollar value to your baby. Then changing it a moment later.
Sometimes you expect a possible counter.
It will feel like an eternity. Many sleepless nights.

Is this how Icarus felt?

You may frequently wonder if you should have stopped earlier or asked for less. The baby is here. Let it be free.
I remounted all the gear. We readjusted the lines.

Take two.
He seemed confident we would try and succeed soon. The red wind socks began to flutter again. This time for a few seconds longer.

Again, my legs started moving forward. Faster now, he ordered. I ran faster, taking extra care not to clip my feet. We ran straight for the cusp of the hill. The valley and trees grew ahead of me.

My furry boots and a web of metal harnesses bounced up and down. The jangle of the metal was eclipsed by the pulse from my chest. I could feel a slight pull on my hips and then shoulders.

Now, the cliff moved too far away from my feet to reach. That was my point of no return.
I felt my legs pull up. Feeling as calm and light as the sky now.
It envelopes you in its heavenly hug.

Art of letting go and not looking back

Before getting on that train, ensure you've made peace with yourself.
When you look down off that edge, it is best to look ahead.
Ensure you don't have some hidden phobias or deep-seated regrets lingering.
Anyone with great anxiety about heights (or fears of bankruptcy) should not step on that deck.

At the moment of truth, your thoughts flash before your eyes.
So don't have those regrets in your heart. I lept (or rather just kept running), looking straight ahead.
Finally, mercifully, thankfully - my transition to air was a glass-off.

Visualize the line, and stick your landing.

In hindsight, some always question whether you could have waited a bit longer, gone higher, or flown further. But in the end, clearly define that landing zone once you decide to exit. Commit to it with everything you can muster for the last push.

Align the best possible lineup for that final position. The North wind controls the rest.

Enjoy the view. Remember the journey.
Luck will always get a dance with success.
IPO in rain or shine.

TopCourt: MasterClass for Tennis - my Covid Startup

Many people got cold feet in the heart of the pandemic.

TopCourt was a perfect example of a pandemic startup - scaling up while the world was shutting down. It rode the e-learning wave when tennis (and the entertainment World) was shuttering its doors.

When the fans couldn't get to the tennis players, we brought tennis players to the fans.
Now broadening to racket sports - it's onto pickleball and introducing those fans to the game. VC money and pro players supporting the rise.

 The Founder (2017) - on Netflix

  • Magic of the Speedee System starts on the Tennis Court with the McDonald Brothers.
  • How Mc'Ds became architect to the World's Most Successful Hamburger Franchise
  • Mortgaging his own home to build the first golden arches.
  • Why Franchise quality control is impossible with too many cooks.


Advice for new founders or board advisors

Meet an international cohort of about 400, while taking 9 courses in the online "mini-MBA" designed to put theory into practice. It is also perfect if you plan to be a product manager or build a startup.

For my 18-month journey from launch to exit, those classes and the online community during the pandemic were my sherpa and North Star. Outside of traveling to Silicon Valley, you can't beat the immersive experience.

For my alumni referral, please use my name, "Jacky Cheong" - part of the Voyager Cohort.

If you get selected within the Workspace app, you can message me! I will help you start your journey like all the sherpas before me.

Learning to smile again

With the altitude and favorable winds, you can take a few pictures or take a few turns to get a full 360 view. It was scary at first to steer. You actually feel better if you feel brave, leaning into the turn with a smile.

At some point, you have to accept the facts:

Gravity has you by the balls. Air doesn't care. Bank accounts weigh nothing.
So just sit back and relax.

As the saying goes...
"Life is short, and so are my legs."
(NIH studies show the benefits of being short)

ABC: Awaken, Begin, and Continue climbing.

I woke up the next morning before sunset.
Everyone was still asleep.
My phone's flashlight guided my way up the trail.

Make Hast. Make your own luck.
Waiting for the first light to set out is a mistake.
You must be up there, ready before the Sun's first rays peek over the ridgeline.

"Before the Birds. Before the Sun"
(- Phil Knight, Shoe Dog)

The sense of discovery and time scarcity spurs me forward.
I love finding a new mountain and capturing blue hour.

When you can rise before the rest, the whole mountain is yours.

You need to have your own faith.
Logos, Karma, Tao. Whatever it is.

Next Episode (Part 3):
  • Getting lost in the beauty of Interlaken
  • Catching more Swiss Trains!
  • Reunion with my Italian friend Cristina from Roma

  • Meeting the largest tennis racket collector in Europe
  • Surviving a bad back on the floor at an Airbnb
  • Nitto and their 700 Euro corporate seats

  • A meeting with fellow tennis travel vlogger, Mr. Tsitsipas
  • My overall impressions of the ATP Finals
  • Trip photos of the Tennis and Travel